If you ever look in the rad fill cap you will see that the factory "cooler" is really nothing more than a single tube that connects the two trans line fittings. Personally I would skip the factory one in the rad (unless you drive in freezing temps and need it to warm up the trans fluid).

I would go a shift kit, auxiliary cooler and whatever rear gears you like (personally I had 3.73s). Don't need the stall converter unless you are needing higher rpm launches. The factory converter will work great for a cruiser. Most aftermarket cams suggest a higher stall converter so that you can maximize the power their cam can produce (most make more power higher in the rpm range and actually kill power down low - hence wanting you to rev up before you get moving).
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Get the largest cooler you can fit in the from fascia. Heat is the worst enemy of an AOD
Call Dan at Silverfox- he will steer you in the right direction. I've run several of his valve bodies. and AOD rebuild kits. A good valve body and a set of 3.73's will wake it up. If the car is fairly stock you can go up to a 2400 or so stall, if HCI or a power adder go to 2800-3200 stall on a converter. I like TCI and Silverfox.

Start here are clickclickracing.com
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I contacted Dan in May, got an auto response listing all of the things he is busy with. His kids, Remodeling a house, Covid etc. and it said if he decided to put you on a wait list for a VB it would be close to 20 weeks.

Just letting you know.
Thanks for your response.

Money is not an issue, and I don't drive everyday so I am not too concerned about gas prices.

Could you elaborate about the part where you said that my engine is stock, and I shouldn't worry about my transmission?
Was drinking when I posted that .
Pay no attention to my rambling.
You do whatever you want to do with your ride.
No bodies business but yours. :)